 |
 |
|
|
| 23/08/1999 | 19:00 | Leeds United | - | Liverpool FC | 1:2 (1:1) | |
| 24/08/1999 | 19:00 | Middlesbrough FC | - | Leicester City | 0:3 (0:2) | |
| 19:00 | Watford FC | - | Aston Villa | 0:1 (0:0) | ||
| 25/08/1999 | 18:45 | Coventry City | - | Manchester United | 1:2 (0:0) | |
| 18:45 | Everton FC | - | Wimbledon FC | 4:0 (1:0) | ||
| 18:45 | Newcastle United | - | Sunderland AFC | 1:2 (1:0) | ||
| 18:45 | Sheffield Wednesday | - | Derby County | 0:2 (0:0) | ||
| 19:00 | Arsenal FC | - | Bradford City | 2:0 (2:0) | ||
| 12/01/2000 | 19:00 | Chelsea FC | - | Tottenham Hotspur | 1:0 (0:0) | |
| 08/03/2000 | 19:00 | West Ham United | - | Southampton FC | 2:0 (1:0) |
| » Tables | Home | Away | First round | Second round | First half | Second half |
| # | Team | M. | W | D | L | goals | Dif. | Pt. | |
|---|---|---|---|---|---|---|---|---|---|
| 1 |
|
Manchester United | 5 | 4 | 1 | 0 | 11:3 | 8 | 13 |
| 2 |
|
Chelsea FC | 5 | 3 | 2 | 0 | 9:3 | 6 | 11 |
| 3 |
|
Aston Villa | 5 | 3 | 1 | 1 | 7:3 | 4 | 10 |
| 4 |
|
Arsenal FC | 5 | 3 | 1 | 1 | 7:4 | 3 | 10 |
|
West Ham United | 5 | 3 | 1 | 1 | 7:4 | 3 | 10 | |
| 6 |
|
Tottenham Hotspur | 5 | 3 | 0 | 2 | 8:6 | 2 | 9 |
| 7 |
|
Liverpool FC | 5 | 3 | 0 | 2 | 5:4 | 1 | 9 |
| 8 |
|
Middlesbrough FC | 5 | 3 | 0 | 2 | 7:7 | 0 | 9 |
| 9 |
|
Everton FC | 5 | 2 | 1 | 2 | 11:8 | 3 | 7 |
| 10 |
|
Leicester City | 5 | 2 | 1 | 2 | 8:6 | 2 | 7 |
| 11 |
|
Leeds United | 5 | 2 | 1 | 2 | 6:5 | 1 | 7 |
| 12 |
|
Sunderland AFC | 5 | 2 | 1 | 2 | 5:7 | -2 | 7 |
| 13 |
|
Watford FC | 5 | 2 | 0 | 3 | 4:6 | -2 | 6 |
| 14 |
|
Southampton FC | 5 | 2 | 0 | 3 | 6:11 | -5 | 6 |
| 15 |
|
Bradford City | 5 | 1 | 2 | 2 | 3:5 | -2 | 5 |
| 16 |
|
Wimbledon FC | 5 | 1 | 2 | 2 | 9:13 | -4 | 5 |
| 17 |
|
Coventry City | 5 | 1 | 1 | 3 | 4:5 | -1 | 4 |
| 18 |
|
Derby County | 5 | 1 | 1 | 3 | 4:7 | -3 | 4 |
| 19 |
|
Newcastle United | 5 | 0 | 1 | 4 | 7:13 | -6 | 1 |
| 20 |
|
Sheffield Wednesday | 5 | 0 | 1 | 4 | 3:11 | -8 | 1 |
